Photocatalytic N‑Methylation of Amines over Pd/TiO2 for the Functionalization of Heterocycles and Pharmaceutical Intermediates
Accepted version
Peer-reviewed
Repository URI
Repository DOI
Change log
Authors
Wheatley, AEH
Wang, Lyu-Ming
Jenkinson, Kellie https://orcid.org/0000-0002-1770-5678
Kuwata, Keiko
Saito, Susumu
Abstract
Amines in heteroaromatic systems and pharmaceutical intermediates were functionalized through N-methylation with methanol using a palladium-loaded titanium dioxide (Pd/TiO2) photocatalyst. This method provides access to a series of tertiary N-methylamines bearing N-, O-, and/or S-containing heteroaromatic functionalities from primary/secondary amines and methanol under mild reaction conditions. Facile syntheses of several pharmaceuticals containing N-methyl or ethyl groups, as well as related deuterated drugs, was achieved through the late-stage functionalization of amines.
Description
Keywords
Green chemistry, Photocatalysis, Methylation, Methanol, Pharmaceuticals
Journal Title
ACS Sustainable Chemistry & Engineering
Conference Name
Journal ISSN
2168-0485
2168-0485
2168-0485
Volume Title
Publisher
American Chemical Society (ACS)
Publisher DOI
Sponsorship
This work was supported by JSPS KAKENHI Grant Number
JP26410115 (H.N.), the Tobe Maki Scholarship Foundation
(H.N.), the JGC-S Scholarship Foundation (H.N.), Fusion Emergent
Research Program from Integrated Research Consortium on
Chemical Sciences (IRCCS, H.N. and A.E.H.W.), the JST ACT-C
program (S.S.), and the UK EPSRC (EP/J500380/1, K.J.).